Celebrate the magic of the season on a festive getaway to Chicago! Enjoy the city’s holiday charm with visits to the Christkindlmarkt, dazzling museum exhibits, and beloved performances like A Christmas Carol at the Goodman Theatre. Stroll through winter flower shows, see sparking light displays, and visit iconic Chicago sights. With cozy holiday spirit at every turn, this Chicago escape is the perfect way to make your season bright.
DAY 1: WELCOME TO CHICAGO!
This evening, meet your Tour Director and friendly travel companions for a Welcome Dinner in Chicago. D
DAY 2: CHICAGO CITY TOUR/CHRISTKINDLMARKT
This morning, explore the Windy City with a local step-on guide. Continue to Chicago’s Christkindlmarkt, filled with unique gifts, tasty treats, and cheerful holiday décor. Tonight, enjoy dinner with your fellow travelers before an evening show. B, D
DAY 3: MUSEUM OF SCIENCE AND INDUSTRY/DEEP DISH PIZZA/A CHRISTMAS CAROL
Begin your day with a visit to the fascinating Museum of Science and Industry, where the annual Christmas Around the World and Holidays of Light exhibit features over 50 beautifully decorated holiday trees. This afternoon, enjoy time on your own to stroll along the Magnificent Mile and explore landmarks such as “The Bean” and the scenic Chicago River. Cap off your evening with a performance of A Christmas Carol at the Goodman Theatre, a holiday tradition beloved by locals and visitors alike. B, L
DAY 4: GARFIELD PARK CONSERVATORY/EVANSTON/LIGHTSCAPE
Visit the Garfield Park Conservatory, one of the nation’s most stunning indoor gardens, where the winter flower show offers a beautiful escape from the chilly weather. Continue on to Evanston, where the Halim Time and Glass Museum offers a fascinating look at one man’s private collection of stained glass and timepieces. As night falls, visit the Chicago Botanic Garden for the spectacular Lightscape display. This magical journey through illuminated installations will transport you to a winter wonderland. B, D
DAY 5: FAREWELL, CHICAGO!
Depart Chicago and travel home with new friends, cherished memories, and the glow of Chicago’s holiday magic. B
Quality Accommodations
Nights 1-4: Hyatt Centric Magnificent Mile, Chicago, IL (or similar)
Dates:
Dec 7-11, 2026
Price Per Person:
Double: $1,897
Single: $2,195
Pre/Post Hotel:
Call for pricing
Optional roundtrip motorcoach transportation from Milwaukee: +$50 per person
Depart/Return:
Chicago, IL
Inclusions:
Welcome Dinner and meals as indicated (B=breakfast, L=lunch, D=dinner)
Fees and tips for included attractions and meals
Luggage handling at most hotels
Free bottled water on coach
24-hour emergency call service
Arrival Time
Our Welcome Dinner on Day 1 is at our hotel starting at 6:30 p.m. We recommend scheduling your flight to arrive by 4:00 p.m.
Departure Time
Schedule your flight home to depart the Chicago any time after breakfast on Day 5.
Walking Distance
To fully enjoy your vacation, you should be in good physical health and understand there are times when a good deal of walking is involved in our tours. Those who have difficulty walking may not want to take this trip or should discuss their personal situation with their doctor before deciding. You should be able to walk at a steady pace up to a mile at a time for a daily total of three to four miles per day and be able to manage steps to board/de-board the motorcoach several times a day. In addition, please know you may be expected to exit the motorcoach at each stop because local law requires mandatory motorcoach driver breaks.
Due to the lack of proper facilities at some of the farms, ranches, and off-the-beaten-path sites we often visit, we are unable to accommodate walkers and wheelchairs.
Average Temps
High of 37° F, low of 25° F
Time Zone
Central
Hotel Amenities
Most accommodations arranged by Country Travel Discoveries are equipped with in-room amenities such as a hair dryer, iron, and coffee maker. In addition, some properties may also have a pool, fitness center, or laundry facilities.
Additional Information
A total of three mailings are sent to assist you in preparing for your tour, including information sent upon receipt of your reservation.
Dress on tour: Dress on tour is casual. Sunscreen, sunglasses, hat, visors, and comfortable walking shoes will add to your enjoyment of this tour. Please pack warm layers for the winter weather.
Travel Protection Available?
Yes, see CountryTravelDiscoveries.com/TravelProtectionPlan
